KR20050044696A - 유기 용매없이 2-(2-니트로페닐아조)페놀을 제조하는 방법 - Google Patents
유기 용매없이 2-(2-니트로페닐아조)페놀을 제조하는 방법 Download PDFInfo
- Publication number
- KR20050044696A KR20050044696A KR1020047008604A KR20047008604A KR20050044696A KR 20050044696 A KR20050044696 A KR 20050044696A KR 1020047008604 A KR1020047008604 A KR 1020047008604A KR 20047008604 A KR20047008604 A KR 20047008604A KR 20050044696 A KR20050044696 A KR 20050044696A
- Authority
- KR
- South Korea
- Prior art keywords
- carbon atoms
- alkyl
- substituted
- straight
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 44
- 230000008569 process Effects 0.000 title claims description 20
- CIVLEPQUPHSEBS-UHFFFAOYSA-N 2-[(2-nitrophenyl)diazenyl]phenol Chemical class OC1=CC=CC=C1N=NC1=CC=CC=C1[N+]([O-])=O CIVLEPQUPHSEBS-UHFFFAOYSA-N 0.000 title description 4
- -1 2-nitrophenylazo Chemical group 0.000 claims abstract description 71
- 150000002989 phenols Chemical class 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 114
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 36
- 125000003342 alkenyl group Chemical group 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 27
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- YNGRGHODNDCZCC-UHFFFAOYSA-N nitro hydrogen sulfate Chemical compound OS(=O)(=O)O[N+]([O-])=O YNGRGHODNDCZCC-UHFFFAOYSA-N 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 14
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 238000005121 nitriding Methods 0.000 claims description 13
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical group [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 12
- 239000004094 surface-active agent Substances 0.000 claims description 11
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 239000013067 intermediate product Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 235000010288 sodium nitrite Nutrition 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 3
- 125000005622 butynylene group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910004013 NO 2 Inorganic materials 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims 1
- 239000006096 absorbing agent Substances 0.000 abstract description 5
- 238000005580 one pot reaction Methods 0.000 abstract description 5
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002243 precursor Substances 0.000 abstract 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 26
- 239000012964 benzotriazole Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 230000009467 reduction Effects 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 238000005859 coupling reaction Methods 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- WMVJWKURWRGJCI-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=C(O)C(C(C)(C)CC)=C1 WMVJWKURWRGJCI-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 150000008365 aromatic ketones Chemical class 0.000 description 4
- 238000006149 azo coupling reaction Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ATXBGHLILIABGX-UHFFFAOYSA-N 2-nitro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O ATXBGHLILIABGX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 239000000538 analytical sample Substances 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- CUVYXWPVMUJMAU-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O CUVYXWPVMUJMAU-UHFFFAOYSA-N 0.000 description 2
- XJMJVLJTEOXUMV-UHFFFAOYSA-N 2-(5-bromobenzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=C(Br)C=CC3=N2)=C1O XJMJVLJTEOXUMV-UHFFFAOYSA-N 0.000 description 2
- POBKADIXKMWDIG-UHFFFAOYSA-N 2-[5-(benzenesulfonyl)benzotriazol-2-yl]-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(N2N=C3C=C(C=CC3=N2)S(=O)(=O)C=2C=CC=CC=2)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 POBKADIXKMWDIG-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- DRPPFIRCBMBJCM-UHFFFAOYSA-N 4-methyl-2-[(2-nitrophenyl)diazenyl]phenol Chemical compound CC1=CC=C(O)C(N=NC=2C(=CC=CC=2)[N+]([O-])=O)=C1 DRPPFIRCBMBJCM-UHFFFAOYSA-N 0.000 description 2
- ZVZFHCZCIBYFMZ-UHFFFAOYSA-N 6-methylheptoxybenzene Chemical compound CC(C)CCCCCOC1=CC=CC=C1 ZVZFHCZCIBYFMZ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000013504 Triton X-100 Substances 0.000 description 2
- 229920004890 Triton X-100 Polymers 0.000 description 2
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 150000001565 benzotriazoles Chemical class 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004979 cyclopentylene group Chemical group 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000007115 recruitment Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- BCCYMYGTHPEHED-UHFFFAOYSA-N 1,2,3,4,5,7,8,9,10,10a-decahydropyrido[1,2-a][1,4]diazepine Chemical compound C1CCNCC2CCCCN21 BCCYMYGTHPEHED-UHFFFAOYSA-N 0.000 description 1
- BCRQVSRWRCLQRV-UHFFFAOYSA-N 1,2-dichloroethane;hydrate Chemical compound O.ClCCCl BCRQVSRWRCLQRV-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- LHCJDXMPHBTIKX-UHFFFAOYSA-N 2,4-bis(2-phenylpropan-2-yl)-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound C=1C(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 LHCJDXMPHBTIKX-UHFFFAOYSA-N 0.000 description 1
- BROKYKIKIWDXKR-UHFFFAOYSA-N 2,4-ditert-butyl-6-(5-dodecylsulfonylbenzotriazol-2-yl)phenol Chemical compound N1=C2C=C(S(=O)(=O)CCCCCCCCCCCC)C=CC2=NN1C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O BROKYKIKIWDXKR-UHFFFAOYSA-N 0.000 description 1
- FXKFDOGNWSKGGJ-UHFFFAOYSA-N 2,4-ditert-butyl-6-(5-fluorobenzotriazol-2-yl)phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(F)C=CC3=N2)=C1O FXKFDOGNWSKGGJ-UHFFFAOYSA-N 0.000 description 1
- ICTNHTYQHAOTNL-UHFFFAOYSA-N 2,4-ditert-butyl-6-(5-octylsulfonylbenzotriazol-2-yl)phenol Chemical compound N1=C2C=C(S(=O)(=O)CCCCCCCC)C=CC2=NN1C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O ICTNHTYQHAOTNL-UHFFFAOYSA-N 0.000 description 1
- VNHBJPHMBDPOJS-UHFFFAOYSA-N 2,4-ditert-butyl-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O VNHBJPHMBDPOJS-UHFFFAOYSA-N 0.000 description 1
- ONEQLWUJQQJEJO-UHFFFAOYSA-N 2-(5-bromobenzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Br)C=CC3=N2)=C1O ONEQLWUJQQJEJO-UHFFFAOYSA-N 0.000 description 1
- OXWHCISICWQZHR-UHFFFAOYSA-N 2-(5-bromobenzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=C(Br)C=CC3=N2)=C1 OXWHCISICWQZHR-UHFFFAOYSA-N 0.000 description 1
- CXAKCASEVOBSIO-UHFFFAOYSA-N 2-(5-bromobenzotriazol-2-yl)-4-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C(N2N=C3C=C(Br)C=CC3=N2)=C1 CXAKCASEVOBSIO-UHFFFAOYSA-N 0.000 description 1
- XAOTULCNDNNDLZ-UHFFFAOYSA-N 2-(5-bromobenzotriazol-2-yl)-4-methylphenol Chemical compound CC1=CC=C(O)C(N2N=C3C=C(Br)C=CC3=N2)=C1 XAOTULCNDNNDLZ-UHFFFAOYSA-N 0.000 description 1
- HGPHUWQJADMWPA-UHFFFAOYSA-N 2-(5-bromobenzotriazol-2-yl)-5-phenylphenol Chemical compound C=1C=C(N2N=C3C=C(Br)C=CC3=N2)C(O)=CC=1C1=CC=CC=C1 HGPHUWQJADMWPA-UHFFFAOYSA-N 0.000 description 1
- DBYVXCLWWUTNPN-UHFFFAOYSA-N 2-(5-bromobenzotriazol-2-yl)-6-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=C(Br)C=CC3=N2)=C(O)C=1C(C)(C)C1=CC=CC=C1 DBYVXCLWWUTNPN-UHFFFAOYSA-N 0.000 description 1
- XKFBJEKWFXADBK-UHFFFAOYSA-N 2-(5-bromobenzotriazol-2-yl)-6-tert-butyl-4-(3-hydroxypropyl)phenol Chemical compound CC(C)(C)C1=CC(CCCO)=CC(N2N=C3C=C(Br)C=CC3=N2)=C1O XKFBJEKWFXADBK-UHFFFAOYSA-N 0.000 description 1
- YBTIWSATJVNXPU-UHFFFAOYSA-N 2-(5-butylsulfonylbenzotriazol-2-yl)-6-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound N1=C2C=C(S(=O)(=O)CCCC)C=CC2=NN1C(C=1O)=CC(C(C)(C)CC(C)(C)C)=CC=1C(C)(C)C1=CC=CC=C1 YBTIWSATJVNXPU-UHFFFAOYSA-N 0.000 description 1
- YATYZLYTTAAVIF-UHFFFAOYSA-N 2-(5-chlorobenzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O YATYZLYTTAAVIF-UHFFFAOYSA-N 0.000 description 1
- ZCYCLXOQGLQFNH-UHFFFAOYSA-N 2-(5-chlorobenzotriazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(N2N=C3C=C(Cl)C=CC3=N2)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 ZCYCLXOQGLQFNH-UHFFFAOYSA-N 0.000 description 1
- OMUFLZDKJGZMRH-UHFFFAOYSA-N 2-(5-chlorobenzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=C(Cl)C=CC3=N2)=C1 OMUFLZDKJGZMRH-UHFFFAOYSA-N 0.000 description 1
- SGHJOQOVLLGIGF-UHFFFAOYSA-N 2-(5-chlorobenzotriazol-2-yl)-4-methylphenol Chemical compound CC1=CC=C(O)C(N2N=C3C=C(Cl)C=CC3=N2)=C1 SGHJOQOVLLGIGF-UHFFFAOYSA-N 0.000 description 1
- UKXUFKKQVZKKAW-UHFFFAOYSA-N 2-(5-chlorobenzotriazol-2-yl)-5-phenylphenol Chemical compound C=1C=C(N2N=C3C=C(Cl)C=CC3=N2)C(O)=CC=1C1=CC=CC=C1 UKXUFKKQVZKKAW-UHFFFAOYSA-N 0.000 description 1
- GSQIWXJOYBPPGF-UHFFFAOYSA-N 2-(5-chlorobenzotriazol-2-yl)-6-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C(O)C=1C(C)(C)C1=CC=CC=C1 GSQIWXJOYBPPGF-UHFFFAOYSA-N 0.000 description 1
- KNTTXLBBKXLUNJ-UHFFFAOYSA-N 2-(5-ethylsulfonylbenzotriazol-2-yl)-6-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound N1=C2C=C(S(=O)(=O)CC)C=CC2=NN1C(C=1O)=CC(C(C)(C)CC(C)(C)C)=CC=1C(C)(C)C1=CC=CC=C1 KNTTXLBBKXLUNJ-UHFFFAOYSA-N 0.000 description 1
- VKZODZGVUYRNQE-UHFFFAOYSA-N 2-(5-fluorobenzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=C(F)C=CC3=N2)=C1O VKZODZGVUYRNQE-UHFFFAOYSA-N 0.000 description 1
- RDTOLUHUJLQOAV-UHFFFAOYSA-N 2-(5-fluorobenzotriazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(N2N=C3C=C(F)C=CC3=N2)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 RDTOLUHUJLQOAV-UHFFFAOYSA-N 0.000 description 1
- CPVQVOPVMGEWSF-UHFFFAOYSA-N 2-(5-fluorobenzotriazol-2-yl)-4-methylphenol Chemical compound CC1=CC=C(O)C(N2N=C3C=C(F)C=CC3=N2)=C1 CPVQVOPVMGEWSF-UHFFFAOYSA-N 0.000 description 1
- UYZDPVUIFSTEJS-UHFFFAOYSA-N 2-(5-fluorobenzotriazol-2-yl)-5-phenylphenol Chemical compound C=1C=C(N2N=C3C=C(F)C=CC3=N2)C(O)=CC=1C1=CC=CC=C1 UYZDPVUIFSTEJS-UHFFFAOYSA-N 0.000 description 1
- AFMNDGDZCQVLFY-UHFFFAOYSA-N 2-(5-fluorobenzotriazol-2-yl)-6-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=C(F)C=CC3=N2)=C(O)C=1C(C)(C)C1=CC=CC=C1 AFMNDGDZCQVLFY-UHFFFAOYSA-N 0.000 description 1
- IMOCDLWVUGQUTC-UHFFFAOYSA-N 2-(5-octylsulfonylbenzotriazol-2-yl)-6-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound N1=C2C=C(S(=O)(=O)CCCCCCCC)C=CC2=NN1C(C=1O)=CC(C(C)(C)CC(C)(C)C)=CC=1C(C)(C)C1=CC=CC=C1 IMOCDLWVUGQUTC-UHFFFAOYSA-N 0.000 description 1
- XDNLOGRBAYJSMQ-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O XDNLOGRBAYJSMQ-UHFFFAOYSA-N 0.000 description 1
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 1
- OLFNXLXEGXRUOI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(N2N=C3C=CC=CC3=N2)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 OLFNXLXEGXRUOI-UHFFFAOYSA-N 0.000 description 1
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 description 1
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- UZUNCLSDTUBVCN-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C(O)C=1C(C)(C)C1=CC=CC=C1 UZUNCLSDTUBVCN-UHFFFAOYSA-N 0.000 description 1
- JFEQQRQRRBZMGE-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-tert-butyl-4-(3-hydroxypropyl)phenol Chemical compound CC(C)(C)C1=CC(CCCO)=CC(N2N=C3C=CC=CC3=N2)=C1O JFEQQRQRRBZMGE-UHFFFAOYSA-N 0.000 description 1
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
- MUSZAXSTSOKYKG-UHFFFAOYSA-N 2-[5-(benzenesulfonyl)benzotriazol-2-yl]-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(C=CC3=N2)S(=O)(=O)C=2C=CC=CC=2)=C1O MUSZAXSTSOKYKG-UHFFFAOYSA-N 0.000 description 1
- DULWULFQPBZNHW-UHFFFAOYSA-N 2-[5-(benzenesulfonyl)benzotriazol-2-yl]-6-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=C(C=CC3=N2)S(=O)(=O)C=2C=CC=CC=2)=C(O)C=1C(C)(C)C1=CC=CC=C1 DULWULFQPBZNHW-UHFFFAOYSA-N 0.000 description 1
- VCMXYOWTQYQUSA-UHFFFAOYSA-N 2-[5-(benzenesulfonyl)benzotriazol-2-yl]-6-tert-butyl-4-(3-hydroxypropyl)phenol Chemical compound CC(C)(C)C1=CC(CCCO)=CC(N2N=C3C=C(C=CC3=N2)S(=O)(=O)C=2C=CC=CC=2)=C1O VCMXYOWTQYQUSA-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- BLYCZGIZZQKNOA-UHFFFAOYSA-N 2-dodecyl-4-methyl-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound CCCCCCCCCCCCC1=CC(C)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O BLYCZGIZZQKNOA-UHFFFAOYSA-N 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- YVVFERCUUGXZLE-UHFFFAOYSA-N 2-tert-butyl-4-(2-hydroxyethyl)-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound CC(C)(C)C1=CC(CCO)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O YVVFERCUUGXZLE-UHFFFAOYSA-N 0.000 description 1
- WIZVALYRXUIVMS-UHFFFAOYSA-N 2-tert-butyl-6-(5-chlorobenzotriazol-2-yl)-4-(3-hydroxypropyl)phenol Chemical compound CC(C)(C)C1=CC(CCCO)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O WIZVALYRXUIVMS-UHFFFAOYSA-N 0.000 description 1
- NTAPWOXBRJBTTQ-UHFFFAOYSA-N 2-tert-butyl-6-(5-fluorobenzotriazol-2-yl)-4-(3-hydroxypropyl)phenol Chemical compound CC(C)(C)C1=CC(CCCO)=CC(N2N=C3C=C(F)C=CC3=N2)=C1O NTAPWOXBRJBTTQ-UHFFFAOYSA-N 0.000 description 1
- UGRZUJILDJHCCR-UHFFFAOYSA-N 2H-benzotriazole 4-phenyl-2H-benzotriazol-5-ol Chemical compound C1=CC=CC2=NNN=C21.OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 UGRZUJILDJHCCR-UHFFFAOYSA-N 0.000 description 1
- SCRHVXDPBPZGRJ-UHFFFAOYSA-N 3-[3-(5-bromobenzotriazol-2-yl)-4-hydroxy-5-(2-phenylpropan-2-yl)phenyl]propanoic acid Chemical compound C=1C(CCC(O)=O)=CC(N2N=C3C=C(Br)C=CC3=N2)=C(O)C=1C(C)(C)C1=CC=CC=C1 SCRHVXDPBPZGRJ-UHFFFAOYSA-N 0.000 description 1
- JPRVWVSGPNILBM-UHFFFAOYSA-N 3-[3-(5-bromobenzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(N2N=C3C=C(Br)C=CC3=N2)=C1O JPRVWVSGPNILBM-UHFFFAOYSA-N 0.000 description 1
- JZNWKSADGODJEK-UHFFFAOYSA-N 3-[3-(5-chlorobenzotriazol-2-yl)-4-hydroxy-5-(2-phenylpropan-2-yl)phenyl]propanoic acid Chemical compound C=1C(CCC(O)=O)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C(O)C=1C(C)(C)C1=CC=CC=C1 JZNWKSADGODJEK-UHFFFAOYSA-N 0.000 description 1
- RLDFKGZXINRWKO-UHFFFAOYSA-N 3-[3-(5-fluorobenzotriazol-2-yl)-4-hydroxy-5-(2-phenylpropan-2-yl)phenyl]propanoic acid Chemical compound C=1C(CCC(O)=O)=CC(N2N=C3C=C(F)C=CC3=N2)=C(O)C=1C(C)(C)C1=CC=CC=C1 RLDFKGZXINRWKO-UHFFFAOYSA-N 0.000 description 1
- OYGYNUPKLMDVHM-UHFFFAOYSA-N 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(N2N=C3C=CC=CC3=N2)=C1O OYGYNUPKLMDVHM-UHFFFAOYSA-N 0.000 description 1
- WPKVPTBBTNIVDN-UHFFFAOYSA-N 3-[3-[5-(benzenesulfonyl)benzotriazol-2-yl]-5-tert-butyl-4-hydroxyphenyl]propanamide Chemical compound CC(C)(C)C1=CC(CCC(N)=O)=CC(N2N=C3C=C(C=CC3=N2)S(=O)(=O)C=2C=CC=CC=2)=C1O WPKVPTBBTNIVDN-UHFFFAOYSA-N 0.000 description 1
- MMPCZTQLVSESIT-UHFFFAOYSA-N 3-[3-tert-butyl-4-hydroxy-5-[5-(trifluoromethyl)benzotriazol-2-yl]phenyl]propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O MMPCZTQLVSESIT-UHFFFAOYSA-N 0.000 description 1
- NFORJTXNUVBLOK-UHFFFAOYSA-N 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O NFORJTXNUVBLOK-UHFFFAOYSA-N 0.000 description 1
- RVZCJXJYENOMTG-UHFFFAOYSA-N 3-[3-tert-butyl-5-(5-fluorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(N2N=C3C=C(F)C=CC3=N2)=C1O RVZCJXJYENOMTG-UHFFFAOYSA-N 0.000 description 1
- VLZRPBFWPDEATD-UHFFFAOYSA-N 3-[4-hydroxy-3-[5-(trifluoromethyl)benzotriazol-2-yl]phenyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCC1=CC=C(O)C(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1 VLZRPBFWPDEATD-UHFFFAOYSA-N 0.000 description 1
- JMKCXYQPSPGNEB-UHFFFAOYSA-N 3-[4-hydroxy-3-[5-(trifluoromethyl)benzotriazol-2-yl]phenyl]propyl prop-2-enoate Chemical compound OC1=CC=C(CCCOC(=O)C=C)C=C1N1N=C2C=C(C(F)(F)F)C=CC2=N1 JMKCXYQPSPGNEB-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- WXQIQASTQGZHBP-UHFFFAOYSA-N 4-(2-hydroxyethyl)-2-(2-phenylpropan-2-yl)-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound C=1C(CCO)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C(O)C=1C(C)(C)C1=CC=CC=C1 WXQIQASTQGZHBP-UHFFFAOYSA-N 0.000 description 1
- YBGAHDSWZZNBNR-UHFFFAOYSA-N 4-(2-hydroxyethyl)-2-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound OCCC1=CC=C(O)C(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1 YBGAHDSWZZNBNR-UHFFFAOYSA-N 0.000 description 1
- KUQMFMAFUWJWAR-UHFFFAOYSA-N 4-(3-hydroxypropyl)-2-(2-phenylpropan-2-yl)-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound C=1C(CCCO)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C(O)C=1C(C)(C)C1=CC=CC=C1 KUQMFMAFUWJWAR-UHFFFAOYSA-N 0.000 description 1
- WMBMNOPFBSLJLS-UHFFFAOYSA-N 4-(3-hydroxypropyl)-2-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound OCCCC1=CC=C(O)C(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1 WMBMNOPFBSLJLS-UHFFFAOYSA-N 0.000 description 1
- KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 description 1
- ZCWBZRBJSPWUPG-UHFFFAOYSA-N 4-bromo-2-nitroaniline Chemical compound NC1=CC=C(Br)C=C1[N+]([O-])=O ZCWBZRBJSPWUPG-UHFFFAOYSA-N 0.000 description 1
- HBILSJNKFHVBOX-UHFFFAOYSA-N 4-dodecyl-2-[(2-nitrophenyl)diazenyl]phenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C(N=NC=2C(=CC=CC=2)[N+]([O-])=O)=C1 HBILSJNKFHVBOX-UHFFFAOYSA-N 0.000 description 1
- BJYNSQZHFWDDKX-UHFFFAOYSA-N 4-dodecyl-2-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1 BJYNSQZHFWDDKX-UHFFFAOYSA-N 0.000 description 1
- XMRFOBNJJKRTSN-UHFFFAOYSA-N 4-nonyl-2-(2-phenylpropan-2-yl)-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound C=1C(CCCCCCCCC)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C(O)C=1C(C)(C)C1=CC=CC=C1 XMRFOBNJJKRTSN-UHFFFAOYSA-N 0.000 description 1
- INKKKAWJTSAIMW-UHFFFAOYSA-N 4-tert-butyl-2-(2-phenylpropan-2-yl)-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound C=1C(C(C)(C)C)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C(O)C=1C(C)(C)C1=CC=CC=C1 INKKKAWJTSAIMW-UHFFFAOYSA-N 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- DGYGESJVCCOGHL-UHFFFAOYSA-N 6-methylheptyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCC(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O DGYGESJVCCOGHL-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YZSBLPWBEDOWSK-UHFFFAOYSA-N C1=CC=CC2=[N+]([O-])NN=C21 Chemical compound C1=CC=CC2=[N+]([O-])NN=C21 YZSBLPWBEDOWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 description 1
- JOGXJLGSRDVVRX-UHFFFAOYSA-N C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=C(C=CC3=N2)S(=O)(=O)C2=CC3=NN(N=C3C=C2)C=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)C(C)(C)C=2C=CC=CC=2)O)=C(O)C=1C(C)(C)C1=CC=CC=C1 Chemical compound C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=C(C=CC3=N2)S(=O)(=O)C2=CC3=NN(N=C3C=C2)C=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)C(C)(C)C=2C=CC=CC=2)O)=C(O)C=1C(C)(C)C1=CC=CC=C1 JOGXJLGSRDVVRX-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SZZWLAZADBEDQP-UHFFFAOYSA-N dimethylcyclopentylene Natural products CC1=C(C)CCC1 SZZWLAZADBEDQP-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- PYDUYOXSXUQLKQ-UHFFFAOYSA-N methyl 3-[3-(5-chlorobenzotriazol-2-yl)-4-hydroxy-5-(2-phenylpropan-2-yl)phenyl]propanoate Chemical compound C=1C(CCC(=O)OC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C(O)C=1C(C)(C)C1=CC=CC=C1 PYDUYOXSXUQLKQ-UHFFFAOYSA-N 0.000 description 1
- VRBLLGLKTUGCSG-UHFFFAOYSA-N methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O VRBLLGLKTUGCSG-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001546 nitrifying effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JMMRXCXRGYLMCA-UHFFFAOYSA-N octyl 3-[3-[5-(benzenesulfonyl)benzotriazol-2-yl]-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=C(C=CC3=N2)S(=O)(=O)C=2C=CC=CC=2)=C1O JMMRXCXRGYLMCA-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 150000004798 β-ketoamides Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/006—Special methods of performing the coupling reaction characterised by process features
- C09B41/009—Diazotising and coupling in one step
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33848401P | 2001-12-05 | 2001-12-05 | |
| US60/338,484 | 2001-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050044696A true KR20050044696A (ko) | 2005-05-12 |
Family
ID=23324996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020047008604A Withdrawn KR20050044696A (ko) | 2001-12-05 | 2002-11-26 | 유기 용매없이 2-(2-니트로페닐아조)페놀을 제조하는 방법 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7074906B2 (https=) |
| EP (1) | EP1451254A1 (https=) |
| JP (1) | JP2005511705A (https=) |
| KR (1) | KR20050044696A (https=) |
| CN (1) | CN100341859C (https=) |
| AU (1) | AU2002356731A1 (https=) |
| BR (1) | BR0214673A (https=) |
| CA (1) | CA2465398A1 (https=) |
| MX (1) | MXPA04005410A (https=) |
| RU (1) | RU2004120783A (https=) |
| WO (1) | WO2003048257A1 (https=) |
| ZA (1) | ZA200403389B (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0225548D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Compounds |
| BR112015022854A2 (pt) | 2013-03-14 | 2017-07-18 | Alkermes Pharma Ireland Ltd | pró-farmacos de fumaratos e uso do mesmo no tratamento de várias doenças |
| US8669281B1 (en) | 2013-03-14 | 2014-03-11 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| CN103193724B (zh) * | 2013-04-08 | 2016-01-13 | 南通大学 | 一种紫外线吸收剂2,2’-亚甲基二[6-(2h-苯并三唑-2-基)-4-叔丁基]苯酚的制备方法 |
| JP6337135B2 (ja) | 2014-02-24 | 2018-06-06 | アルカーメス ファーマ アイルランド リミテッド | フマル酸エステルのスルホンアミドプロドラッグ及びスルフィンアミドプロドラッグ並びに種々の疾患の治療におけるその使用 |
| CN103965125A (zh) * | 2014-05-06 | 2014-08-06 | 西安近代化学研究所 | 一种3,3’-二硝基-5,5’-联-1,2,4-三唑的合成方法 |
| CN112679979B (zh) * | 2020-12-29 | 2023-09-01 | 浙江永合新材料科技有限公司 | 一种苯并三唑类紫外线吸收剂中间体偶氮染料的制备方法 |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2362988A (en) | 1940-11-26 | 1944-11-21 | Geigy Ag J R | Mordant triazole dyestuffs and process for making the same |
| US2418416A (en) | 1943-12-30 | 1947-04-01 | Du Pont | Manufacture of azo lakes |
| US2478767A (en) | 1945-10-04 | 1949-08-09 | Du Pont | Manufacture of azo compounds |
| US2478768A (en) | 1945-10-04 | 1949-08-09 | Du Pont | Manufacture of azo lakes |
| US3773751A (en) | 1969-09-08 | 1973-11-20 | American Cyanamid Co | Synthesis of nitroaromatic-azophenols |
| US3793305A (en) | 1970-09-14 | 1974-02-19 | Du Pont | One-step process of preparing azo dyes by simultaneous diazotization |
| CH573400A5 (https=) * | 1972-07-11 | 1976-03-15 | Ciba Geigy Ag | |
| US3998804A (en) * | 1972-07-11 | 1976-12-21 | Ciba-Geigy Corporation | Process for coupling of water-insoluble 2,4-disubstituted phenols with diazotized o-nitroanilines |
| US3978074A (en) | 1973-11-21 | 1976-08-31 | Uniroyal Inc. | Method of making hydroxyarylbenzotriazoles and their N-oxides |
| DE2503714C3 (de) | 1975-01-30 | 1978-05-03 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von wasserlöslichen Azofarbstoffen |
| DE2516032C2 (de) * | 1975-04-12 | 1984-10-04 | Bayer Ag, 5090 Leverkusen | Verfahren zum Diazotieren aromatischer Amine |
| JPS52113974A (en) | 1976-03-19 | 1977-09-24 | Kawaken Fine Chem Co Ltd | Synthesis of benzotriazole derivatives |
| JPS52113973A (en) | 1976-03-19 | 1977-09-24 | Kawaken Fine Chem Co Ltd | Synthesis of benzotriazole derivatives |
| JPS5398932A (en) * | 1977-02-04 | 1978-08-29 | Hitachi Chem Co Ltd | Preparation of o-nitro-o'-hydroxyazobenzenes and 2-(2'-hydroxyphenyl)- 1,2,3-benzotriazoles |
| US4219480A (en) | 1977-09-20 | 1980-08-26 | Ciba-Geigy Corporation | Process for the production of 2-aryl-2H-benzotriazoles |
| US4230867A (en) * | 1977-11-25 | 1980-10-28 | Ciba-Geigy Corporation | Process for the production of 2-aryl-2H-benzotriazoles |
| EP0006564B1 (de) * | 1978-06-26 | 1981-12-30 | Ciba-Geigy Ag | 2-(2-Hydroxy-3.5-disubstituiertes-phenyl)-2H-benzotriazol und damit stabilisierte Mischungen |
| EP0034836B1 (de) * | 1979-05-16 | 1983-07-13 | Ciba-Geigy Ag | Verfahren zum Herstellen von Nitroazobenzolen |
| US4226763A (en) * | 1978-06-26 | 1980-10-07 | Ciba-Geigy Corporation | 2-[2-Hydroxy-3,5-di-(.alpha.,α-dimethylbenzyl)-phenyl]-2H-benzotriazole and stabilized compositions |
| US4347180A (en) * | 1979-05-16 | 1982-08-31 | Ciba-Geigy Corporation | High caustic coupling process for preparing substituted 2-nitro-2'-hydroxyazobenzenes |
| JPS56133076A (en) | 1980-03-25 | 1981-10-17 | Nissan Motor Co Ltd | Painting method of intermediate coat |
| JPS59170172A (ja) | 1983-03-18 | 1984-09-26 | Shuichi Seino | ２−フエニルベンゾトリアゾ−ル類の製造方法 |
| CH655125A5 (de) * | 1983-09-21 | 1986-03-27 | Ciba Geigy Ag | Verfahren zur herstellung von azofarbstoffpraeparaten. |
| EP0257151B1 (en) | 1986-08-22 | 1992-01-29 | Chemipro Kasei Kaisha, Ltd. | Method for preparing 2-phenylbenzotriazoles and 2-phenylbenzotriazole-n-oxides |
| JPS61197571A (ja) | 1985-02-27 | 1986-09-01 | Kemipuro Kasei Kk | ２−フエニルベンゾトリアゾ−ル−ｎ−オキシド類の製造法 |
| US4789541A (en) | 1985-10-04 | 1988-12-06 | Davis Michael H | Method and composition for in vivo radiolabeling of red blood cells with 99m Tc |
| JPH0798812B2 (ja) | 1986-09-16 | 1995-10-25 | ケミプロ化成株式会社 | ２−フエニルベンゾトリアゾ−ル類の製造法 |
| JPH0798811B2 (ja) | 1986-09-16 | 1995-10-25 | ケミプロ化成株式会社 | ２−フエニルベンゾトリアゾ−ル−ｎ−オキシド類の製造法 |
| JPH0788595B2 (ja) | 1987-01-27 | 1995-09-27 | ケミプロ化成株式会社 | ２−フエニルベンゾトリアゾ−ル類の製造方法 |
| JPH02202879A (ja) | 1989-01-31 | 1990-08-10 | Kemipuro Kasei Kk | ２―フェニルベンゾトリアゾール類の製造法 |
| JPH02202880A (ja) | 1989-01-31 | 1990-08-10 | Kemipuro Kasei Kk | ２―フェニルベンゾトリアゾール類の製造法 |
| KR100313583B1 (ko) * | 1993-09-16 | 2002-11-23 | 시바 스페셜티 케미칼스 홀딩 인크. | 2,4-이중치환된 페놀과 2-니트로아닐린의 아조커플링 |
| US5571924A (en) | 1995-07-12 | 1996-11-05 | Ciba-Geigy Corporation | Process for the preparation of benzotriazoles |
| US6166218A (en) * | 1996-11-07 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Benzotriazole UV absorbers having enhanced durability |
| US6566507B2 (en) * | 2000-08-03 | 2003-05-20 | Ciba Specialty Chemicals Corporation | Processes for the preparation of benzotriazole UV absorbers |
-
2002
- 2002-11-26 WO PCT/EP2002/013292 patent/WO2003048257A1/en not_active Ceased
- 2002-11-26 JP JP2003549440A patent/JP2005511705A/ja active Pending
- 2002-11-26 CA CA002465398A patent/CA2465398A1/en not_active Abandoned
- 2002-11-26 CN CNB028242904A patent/CN100341859C/zh not_active Expired - Fee Related
- 2002-11-26 AU AU2002356731A patent/AU2002356731A1/en not_active Abandoned
- 2002-11-26 MX MXPA04005410A patent/MXPA04005410A/es not_active Application Discontinuation
- 2002-11-26 KR KR1020047008604A patent/KR20050044696A/ko not_active Withdrawn
- 2002-11-26 US US10/497,621 patent/US7074906B2/en not_active Expired - Fee Related
- 2002-11-26 RU RU2004120783/04A patent/RU2004120783A/ru not_active Application Discontinuation
- 2002-11-26 BR BR0214673-8A patent/BR0214673A/pt not_active IP Right Cessation
- 2002-11-26 EP EP02804196A patent/EP1451254A1/en not_active Withdrawn
-
2004
- 2004-05-05 ZA ZA200403389A patent/ZA200403389B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1451254A1 (en) | 2004-09-01 |
| US20050053562A1 (en) | 2005-03-10 |
| MXPA04005410A (es) | 2004-10-11 |
| ZA200403389B (en) | 2006-06-28 |
| RU2004120783A (ru) | 2006-01-10 |
| CN100341859C (zh) | 2007-10-10 |
| CN1599777A (zh) | 2005-03-23 |
| US7074906B2 (en) | 2006-07-11 |
| AU2002356731A1 (en) | 2003-06-17 |
| CA2465398A1 (en) | 2003-06-12 |
| WO2003048257A1 (en) | 2003-06-12 |
| JP2005511705A (ja) | 2005-04-28 |
| BR0214673A (pt) | 2004-10-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6566507B2 (en) | Processes for the preparation of benzotriazole UV absorbers | |
| KR20050044696A (ko) | 유기 용매없이 2-(2-니트로페닐아조)페놀을 제조하는 방법 | |
| US4780541A (en) | Method for preparing 2-phenylbenzotriazoles and 2-phenylbenzotriazole-N-oxides | |
| US5675015A (en) | Process for the preparation of benzotriazole derivatives | |
| US5670654A (en) | Method of synthesizing 2-(2'-hydroxyphenyl) benzotriazole compounds | |
| US5808086A (en) | Process for preparing bis (2-hydroxyphenyl-3-benztriazole) methanes | |
| US4734532A (en) | Process for the preparation of 4,4'-dinitrodibenzyls | |
| US5739348A (en) | Method of synthesizing tert-amido-substituted 2-(2'-hydroxyphenyl) benzotriazole compounds in a one-step process | |
| CA1241659A (en) | Method for producing a 2-phenylbenzotriazole | |
| US5436322A (en) | Azo coupling of 2-nitroanilines with 2,4,-disbustituted phenols | |
| EP3604288B1 (en) | Regioselective one-step process for synthesizing 2-hydroxyquinoxaline | |
| US4749813A (en) | 4-alkyl-2-trifluoromethylanilines | |
| US7358397B2 (en) | Preparation of halogenated 4-aminophenols | |
| US6353113B1 (en) | Process for the preparation of 5-perfluoroalkyl substituted benzotriazole UV absorbers | |
| US4095024A (en) | Process for the manufacture of 1-aryl-3-carboxypyrazolid-5-ones | |
| US4281143A (en) | Process for preparing 1-aryl-3-amino-5-pyrazolones | |
| EP0259530B1 (en) | Method for preparing 2-phenylbenzotriazoles and 2-phenylbenzotriazole-n-oxides | |
| RU2163611C2 (ru) | СПОСОБ ПОЛУЧЕНИЯ 1-(n-R-ФЕНИЛАЗО)-3-НИТРОНАФТАЛИНОВ | |
| US5122612A (en) | Process for producing 5-amino-4-halogeno-1h-pyrazole compounds | |
| CA1168655A (en) | 2-[2-HYDROXY-3,5-DI-(.alpha.,.alpha.-DI-METHYLBENZYL) PHENYL]- 2H-BENZOTRIAZOLES AND STABILIZED COMPOSITIONS | |
| DE1803636B2 (de) | Verfahren zur herstellung von arylotriazolen | |
| GB2080287A (en) | 2-Alkoxy-5-aminobenzene Sulfonates and 5-Diazo Derivatives thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20040604 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |